Volume 90, 27 January 2015, Pages 491-496
a
Laboratory of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Barcelona, Av. Diagonal 643, Barcelona, Spain
b Department of Biochemistry and Molecular Biology, Faculty of Biology, University of Barcelona, Barcelona, Spain
c Oryzon, Parc Cientific de Barcelona, Baldiri Reixac 12, Barcelona, Spain
b Department of Biochemistry and Molecular Biology, Faculty of Biology, University of Barcelona, Barcelona, Spain
c Oryzon, Parc Cientific de Barcelona, Baldiri Reixac 12, Barcelona, Spain
Abstract
The aqueous
extraction of the sesquiterpene lactone xanthatin from Xanthium spinosum
L. favours the conversion of xanthinin (1) to xanthatin (2) via the
loss of acetic acid. The cytotoxic (Hep-G2 and L1210 human cell lines)
and antiviral activities of isolated xanthatin are established. This
natural compound shows significant cytotoxicity against the Hep-G2 cell
line and our experimental results reveal its strong anti-angiogenesis
capacity in vitro. The structure of xanthatin is determined by
spectroscopic methods and for the first time confirmed by X-ray
diffraction. © 2014 Elsevier Masson SAS. All rights reserved.
Author keywords
Anti-angiogenesis; Antitumor activity; Antiviral activity; Sesquiterpene lactones; Xanthatin; Xanthium spinosum L
Indexed keywords
EMTREE drug terms: 4 acetamido 5 amino 3 (1
ethylpropoxy) 1 cyclohexene 1 carboxylic acid; 5 (2 bromovinyl) 2'
deoxyuridine; acetic acid; amantadine; angiogenesis inhibitor; antivirus
agent; caffeic acid; ciclofovir; ganciclovir; paclitaxel; plant medicinal
product; ribavirin; rimantadine; sesquiterpene lactone derivative;
unclassified drug; xanthatin; xanthinin; angiogenesis inhibitor;
antivirus agent; cytotoxic agent; plant extract; Xanthium spinosum extract
EMTREE medical terms: animal cell; antiangiogenic
activity; antiproliferative activity; antiviral activity; aqueous
solution; Article; carbon nuclear magnetic resonance; cell
proliferation; controlled study; crystal structure; cytotoxicity; drug
isolation; female; HeLa cell line; HepG2 cell line; human; human cell;
human cell culture; IC50; in vitro study; infrared spectroscopy; L1210
cell line; mass spectrometry; medicinal plant;
nonhuman; process optimization; proton nuclear magnetic resonance;
virus strain; X ray crystallography; X ray diffraction; Xanthium;
Xanthium spinosum; Coronavirus; Coxsackie virus B4; feline corona virus; feline
herpes virus; Herpes simplex virus 1; Herpes simplex virus 2; Human
respiratory syncytial virus; influenza A (H1N1); influenza A (H3N2);
influenza B; Parainfluenza virus 3; Punta Toro virus; repvirus 1;
Sindbis virus; Vaccinia virus; Varicella zoster virus; Vesiculovirus
Chemicals and CAS Registry Numbers: 4 acetamido 5 amino
3 (1 ethylpropoxy) 1 cyclohexene 1 carboxylic acid, 187227-45-8; 5 (2
bromovinyl) 2' deoxyuridine, 69304-47-8, 82768-44-3; acetic acid,
127-08-2, 127-09-3, 64-19-7, 71-50-1; amantadine, 665-66-7, 768-94-5;
caffeic acid, 27323-69-9, 331-39-5; ganciclovir, 82410-32-0; paclitaxel,
33069-62-4; ribavirin, 36791-04-5; rimantadine, 13392-28-4, 1501-84-4
ISSN: 02235234
CODEN: EJMCASource Type: Journal
Original language: English
DOI: 10.1016/j.ejmech.2014.11.060Document Type: Article
Publisher: Elsevier Masson SAS
